organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2a,3a-Di­hydroxy­androstan-16-one

aInstitute of Materia Medica, Chinese Academy of Medical Sciences, and Peking Union Medical College, 1 Xiannong Tan Street, Beijing 100050, People's Republic of China, and bState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, Yunnan, People's Republic of China
*Correspondence e-mail: luy@imm.ac.cn

(Received 24 June 2009; accepted 24 July 2009; online 31 July 2009)

The title compound, C19H28O4, is a new androstane steroid derivative. In the crystal, mol­ecules are linked along the a axis by inter­molecular O—H⋯O hydrogen bonds.

Related literature

The title compound was obtained from the methanol extract of stems of Trichilia claussenii by column chromatograph, see: Pupo et al. (1997[Pupo, M. T., Vieira, P. C., Fernandes, J. B., da Silva, M. F. & Fo, R. E. (1997). Phytochemistry, 45, 1495-1500.]). It shows strong insecticidal activity, see: Champagne et al. (1992[Champagne, D. E., Koul, O., Isman, M. B., Scudder, G. G. E. & Towers, G. H. N. (1992). Phytochemistry, 31, 377-394.]).

[Scheme 1]

Experimental

Crystal data
  • C19H28O4

  • Mr = 320.41

  • Monoclinic, P 21

  • a = 10.8687 (2) Å

  • b = 6.3379 (1) Å

  • c = 12.9038 (2) Å

  • β = 112.882 (1)°

  • V = 818.93 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 295 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • MAC DIP 2030K diffractometer

  • Absorption correction: none

  • 2065 measured reflections

  • 2065 independent reflections

  • 1929 reflections with I > 2σ(I)

  • Rint = 0.015

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.105

  • S = 1.14

  • 2065 reflections

  • 208 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2A⋯O1i 0.82 2.03 2.8088 (19) 158
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+1].

Data collection: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound,(I), was yielded from the methanol extract of stems of Trichilia claussenii by column chromatographies (Pupo et al., 1997) and recrystasllized from methanol-hexane(1:1). As it shows strong biological activities against insects (Champagne et al., 1992) we have determined its crystal stucture, Fig. 1, Table 1.

In this structure, rings A,B and C adopt chair conformations, and both ring D,E adopt envelope conformations. The dihedral angle between the least-squares plane through the 6 atoms of rings A and B is 9.2 (1)°, and that between rings B and C and that between rings C and D are 175.0 (2)° and 2.5 (1)°, respectively.

Besides, the molecules of the title compound are linked into each other along a axis, by intermolecular hydrogen bonds O—H···O. Atom O2 acts as hydrogen-bond donor to atom O1 at (-x, y + 1/2, -z + 1). Molecules pack in ribbons along the b axis, Fig. 2.

Related literature top

The title compound was obtained from the methanol extract of stems of Trichilia claussenii by column chromatograph, see: Pupo et al. (1997). It shows strong insecticidal activity, see: Champagne et al. (1992);

Experimental top

The title compound was prepared according to the procedure of extracting Trichilia claussenii (Pupo et al., 1997). At the temprature of 283 K and unventilated condition, single crystals of (I) were obtained from mixed solvent of methanol-hexane(1:1) within two weeks.

Refinement top

In the absence of significant anomalous dispersion effects, Freidel pairs were merged. The position of the hydroxy H atoms were refined freely along with an isotropic displacement parameter Uiso(H)= 1.2Ueq(C). The methyl H atoms were then constrained to an ideal geometry with C—H distances of 0.96 Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C—C bond. All the other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances in the range of 0.92–0.98 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the molecule showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing of (I) viewed down the b axis.
2a,3a-Dihydroxyandrostan-16-one top
Crystal data top
C19H28O4F(000) = 348
Mr = 320.41Dx = 1.299 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2065 reflections
a = 10.8687 (2) Åθ = 1.7–27.6°
b = 6.3379 (1) ŵ = 0.09 mm1
c = 12.9038 (2) ÅT = 295 K
β = 112.882 (1)°Block, colourless
V = 818.93 (2) Å30.20 × 0.20 × 0.20 mm
Z = 2
Data collection top
MAC DIP 2030K
diffractometer
1929 reflections with I > 2σ(I)
Radiation source: rotate anodeRint = 0.015
Graphite monochromatorθmax = 27.6°, θmin = 1.7°
Detector resolution: 0 pixels mm-1h = 1413
ω scansk = 08
2065 measured reflectionsl = 016
2065 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0593P)2 + 0.0933P]
where P = (Fo2 + 2Fc2)/3
2065 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.26 e Å3
1 restraintΔρmin = 0.15 e Å3
Crystal data top
C19H28O4V = 818.93 (2) Å3
Mr = 320.41Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.8687 (2) ŵ = 0.09 mm1
b = 6.3379 (1) ÅT = 295 K
c = 12.9038 (2) Å0.20 × 0.20 × 0.20 mm
β = 112.882 (1)°
Data collection top
MAC DIP 2030K
diffractometer
1929 reflections with I > 2σ(I)
2065 measured reflectionsRint = 0.015
2065 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.105H-atom parameters constrained
S = 1.14Δρmax = 0.26 e Å3
2065 reflectionsΔρmin = 0.15 e Å3
208 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.10604 (14)0.6665 (3)0.44798 (11)0.0387 (3)
O20.09261 (16)1.0230 (3)0.48050 (15)0.0530 (5)
H2A0.02211.04260.48820.080*
O30.09685 (18)1.0625 (3)0.25157 (18)0.0597 (5)
H3A0.17551.06670.20830.089*
O40.61221 (19)0.0525 (4)0.09632 (16)0.0657 (5)
C10.17314 (18)0.9035 (3)0.34250 (16)0.0321 (4)
H1A0.26100.93940.39760.038*
H1B0.14431.01130.28460.038*
C20.07349 (19)0.8750 (3)0.39679 (18)0.0371 (4)
C30.0693 (2)0.8638 (4)0.3084 (2)0.0423 (5)
H3B0.13140.84110.34570.051*
C40.08066 (18)0.6822 (4)0.22815 (18)0.0419 (5)
H4B0.16220.69990.16180.050*
H4C0.08860.55160.26420.050*
C50.03684 (17)0.6613 (4)0.19065 (15)0.0337 (4)
H5A0.03000.77630.13790.040*
C60.02645 (19)0.4533 (4)0.12841 (17)0.0418 (5)
H6A0.02080.33830.17600.050*
H6B0.05500.45330.06110.050*
C70.14492 (19)0.4159 (4)0.09552 (16)0.0425 (5)
H7A0.14360.51950.03980.051*
H7B0.13710.27710.06180.051*
C80.27756 (17)0.4311 (3)0.19700 (14)0.0294 (4)
H8A0.28070.32020.25090.035*
C90.28860 (17)0.6477 (3)0.25428 (14)0.0278 (4)
H90.27770.75300.19580.033*
C100.17217 (16)0.6848 (3)0.29237 (14)0.0273 (4)
C110.42783 (17)0.6878 (4)0.34704 (16)0.0357 (4)
H11A0.43250.83310.37200.043*
H11B0.43900.59780.41090.043*
C120.54289 (19)0.6468 (3)0.30905 (19)0.0383 (5)
H12A0.53990.74920.25230.046*
H12B0.62750.66250.37250.046*
C130.53218 (18)0.4254 (3)0.26115 (15)0.0314 (4)
C140.39575 (18)0.4035 (3)0.16258 (15)0.0311 (4)
H140.39030.51910.11050.037*
C150.4097 (2)0.2001 (4)0.10396 (17)0.0429 (5)
H15A0.38180.07830.13490.051*
H15B0.35720.20690.02370.051*
C160.5576 (2)0.1902 (5)0.12818 (18)0.0455 (5)
C170.6267 (2)0.3747 (4)0.2021 (2)0.0451 (5)
H17A0.63480.49340.15770.054*
H17B0.71470.33570.25580.054*
C180.5558 (2)0.2595 (4)0.35272 (18)0.0428 (5)
H18A0.49710.28570.39100.064*
H18B0.64680.26670.40560.064*
H18C0.53820.12170.31920.064*
C190.17183 (18)0.5448 (3)0.39026 (15)0.0314 (4)
H19A0.12390.41440.36170.038*
H19B0.26240.51080.44060.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0390 (7)0.0436 (8)0.0434 (7)0.0018 (7)0.0270 (6)0.0048 (7)
O20.0462 (9)0.0557 (11)0.0714 (10)0.0022 (8)0.0384 (8)0.0216 (9)
O30.0445 (9)0.0469 (10)0.0889 (13)0.0149 (8)0.0274 (9)0.0156 (10)
O40.0664 (11)0.0689 (13)0.0684 (11)0.0217 (10)0.0334 (9)0.0171 (10)
C10.0285 (8)0.0285 (10)0.0453 (10)0.0002 (7)0.0209 (8)0.0004 (8)
C20.0349 (10)0.0361 (11)0.0491 (11)0.0015 (8)0.0260 (9)0.0001 (9)
C30.0313 (10)0.0423 (12)0.0615 (13)0.0066 (9)0.0271 (10)0.0073 (11)
C40.0241 (9)0.0481 (12)0.0516 (11)0.0003 (9)0.0128 (8)0.0063 (11)
C50.0270 (8)0.0364 (10)0.0349 (8)0.0024 (8)0.0088 (7)0.0054 (9)
C60.0275 (9)0.0485 (13)0.0389 (10)0.0027 (9)0.0015 (8)0.0040 (9)
C70.0374 (10)0.0499 (13)0.0332 (9)0.0025 (10)0.0062 (8)0.0093 (10)
C80.0299 (8)0.0310 (9)0.0274 (8)0.0005 (7)0.0113 (7)0.0021 (7)
C90.0274 (8)0.0281 (9)0.0321 (8)0.0000 (7)0.0160 (7)0.0019 (7)
C100.0249 (8)0.0268 (8)0.0326 (8)0.0000 (7)0.0138 (6)0.0033 (7)
C110.0277 (8)0.0367 (10)0.0460 (10)0.0052 (8)0.0177 (8)0.0122 (9)
C120.0307 (9)0.0337 (11)0.0563 (12)0.0050 (8)0.0235 (9)0.0087 (9)
C130.0309 (9)0.0295 (9)0.0386 (9)0.0002 (8)0.0187 (8)0.0001 (8)
C140.0377 (9)0.0296 (10)0.0289 (8)0.0043 (8)0.0162 (7)0.0018 (8)
C150.0490 (11)0.0444 (12)0.0359 (9)0.0057 (11)0.0173 (9)0.0081 (9)
C160.0533 (12)0.0482 (13)0.0422 (10)0.0127 (11)0.0264 (9)0.0016 (11)
C170.0426 (11)0.0412 (12)0.0630 (13)0.0060 (10)0.0331 (10)0.0001 (11)
C180.0453 (12)0.0409 (11)0.0363 (10)0.0043 (9)0.0093 (9)0.0064 (9)
C190.0308 (8)0.0320 (10)0.0352 (9)0.0006 (8)0.0171 (7)0.0054 (8)
Geometric parameters (Å, º) top
O1—C191.440 (2)C8—H8A0.9800
O1—C21.458 (3)C9—C111.542 (2)
O2—C21.384 (3)C9—C101.543 (2)
O2—H2A0.8200C9—H90.9800
O3—C31.429 (3)C10—C191.545 (2)
O3—H3A0.8200C11—C121.533 (2)
O4—C161.214 (3)C11—H11A0.9700
C1—C21.512 (2)C11—H11B0.9700
C1—C101.528 (3)C12—C131.519 (3)
C1—H1A0.9700C12—H12A0.9700
C1—H1B0.9700C12—H12B0.9700
C2—C31.529 (3)C13—C181.527 (3)
C3—C41.521 (4)C13—C171.532 (3)
C3—H3B0.9800C13—C141.539 (3)
C4—C51.537 (3)C14—C151.532 (3)
C4—H4B0.9700C14—H140.9800
C4—H4C0.9700C15—C161.515 (3)
C5—C61.525 (3)C15—H15A0.9700
C5—C101.551 (2)C15—H15B0.9700
C5—H5A0.9800C16—C171.512 (4)
C6—C71.523 (3)C17—H17A0.9700
C6—H6A0.9700C17—H17B0.9700
C6—H6B0.9700C18—H18A0.9600
C7—C81.528 (2)C18—H18B0.9600
C7—H7A0.9700C18—H18C0.9600
C7—H7B0.9700C19—H19A0.9700
C8—C141.524 (2)C19—H19B0.9700
C8—C91.542 (3)
C19—O1—C2109.44 (13)C1—C10—C9113.66 (15)
C2—O2—H2A109.5C1—C10—C19100.18 (14)
C3—O3—H3A109.5C9—C10—C19115.84 (14)
C2—C1—C10101.51 (15)C1—C10—C5107.06 (15)
C2—C1—H1A111.5C9—C10—C5109.94 (13)
C10—C1—H1A111.5C19—C10—C5109.50 (15)
C2—C1—H1B111.5C12—C11—C9113.59 (15)
C10—C1—H1B111.5C12—C11—H11A108.8
H1A—C1—H1B109.3C9—C11—H11A108.8
O2—C2—O1108.94 (16)C12—C11—H11B108.8
O2—C2—C1111.31 (17)C9—C11—H11B108.8
O1—C2—C1103.11 (15)H11A—C11—H11B107.7
O2—C2—C3114.50 (17)C13—C12—C11110.12 (16)
O1—C2—C3107.03 (17)C13—C12—H12A109.6
C1—C2—C3111.22 (16)C11—C12—H12A109.6
O3—C3—C4111.86 (18)C13—C12—H12B109.6
O3—C3—C2106.94 (18)C11—C12—H12B109.6
C4—C3—C2109.48 (16)H12A—C12—H12B108.2
O3—C3—H3B109.5C12—C13—C18110.98 (17)
C4—C3—H3B109.5C12—C13—C17115.81 (17)
C2—C3—H3B109.5C18—C13—C17107.28 (17)
C3—C4—C5114.94 (17)C12—C13—C14108.43 (16)
C3—C4—H4B108.5C18—C13—C14113.29 (16)
C5—C4—H4B108.5C17—C13—C14100.79 (15)
C3—C4—H4C108.5C8—C14—C15119.80 (17)
C5—C4—H4C108.5C8—C14—C13113.53 (13)
H4B—C4—H4C107.5C15—C14—C13103.60 (15)
C6—C5—C4109.85 (17)C8—C14—H14106.3
C6—C5—C10112.35 (16)C15—C14—H14106.3
C4—C5—C10110.84 (14)C13—C14—H14106.3
C6—C5—H5A107.9C16—C15—C14103.53 (19)
C4—C5—H5A107.9C16—C15—H15A111.1
C10—C5—H5A107.9C14—C15—H15A111.1
C7—C6—C5112.59 (18)C16—C15—H15B111.1
C7—C6—H6A109.1C14—C15—H15B111.1
C5—C6—H6A109.1H15A—C15—H15B109.0
C7—C6—H6B109.1O4—C16—C17125.6 (2)
C5—C6—H6B109.1O4—C16—C15125.4 (3)
H6A—C6—H6B107.8C17—C16—C15108.98 (18)
C6—C7—C8111.69 (15)C16—C17—C13102.17 (17)
C6—C7—H7A109.3C16—C17—H17A111.3
C8—C7—H7A109.3C13—C17—H17A111.3
C6—C7—H7B109.3C16—C17—H17B111.3
C8—C7—H7B109.3C13—C17—H17B111.3
H7A—C7—H7B107.9H17A—C17—H17B109.2
C14—C8—C7111.37 (14)C13—C18—H18A109.5
C14—C8—C9108.93 (15)C13—C18—H18B109.5
C7—C8—C9109.80 (16)H18A—C18—H18B109.5
C14—C8—H8A108.9C13—C18—H18C109.5
C7—C8—H8A108.9H18A—C18—H18C109.5
C9—C8—H8A108.9H18B—C18—H18C109.5
C8—C9—C11112.89 (15)O1—C19—C10105.95 (16)
C8—C9—C10111.57 (15)O1—C19—H19A110.5
C11—C9—C10113.97 (14)C10—C19—H19A110.5
C8—C9—H9105.9O1—C19—H19B110.5
C11—C9—H9105.9C10—C19—H19B110.5
C10—C9—H9105.9H19A—C19—H19B108.7
C19—O1—C2—O2142.16 (15)C4—C5—C10—C160.1 (2)
C19—O1—C2—C123.84 (19)C6—C5—C10—C952.7 (2)
C19—O1—C2—C393.54 (17)C4—C5—C10—C9176.02 (17)
C10—C1—C2—O2158.11 (16)C6—C5—C10—C1975.65 (19)
C10—C1—C2—O141.46 (17)C4—C5—C10—C1947.7 (2)
C10—C1—C2—C372.9 (2)C8—C9—C11—C1250.3 (2)
O2—C2—C3—O364.1 (2)C10—C9—C11—C12178.96 (17)
O1—C2—C3—O3175.03 (16)C9—C11—C12—C1354.3 (2)
C1—C2—C3—O363.1 (2)C11—C12—C13—C1867.1 (2)
O2—C2—C3—C4174.50 (18)C11—C12—C13—C17170.30 (18)
O1—C2—C3—C453.7 (2)C11—C12—C13—C1457.9 (2)
C1—C2—C3—C458.3 (2)C7—C8—C14—C1559.0 (2)
O3—C3—C4—C575.6 (2)C9—C8—C14—C15179.72 (16)
C2—C3—C4—C542.7 (2)C7—C8—C14—C13177.94 (17)
C3—C4—C5—C6169.86 (18)C9—C8—C14—C1356.7 (2)
C3—C4—C5—C1045.1 (2)C12—C13—C14—C861.8 (2)
C4—C5—C6—C7176.24 (17)C18—C13—C14—C861.8 (2)
C10—C5—C6—C752.4 (2)C17—C13—C14—C8176.12 (17)
C5—C6—C7—C854.4 (3)C12—C13—C14—C15166.64 (15)
C6—C7—C8—C14177.36 (19)C18—C13—C14—C1569.71 (19)
C6—C7—C8—C956.6 (2)C17—C13—C14—C1544.6 (2)
C14—C8—C9—C1149.58 (18)C8—C14—C15—C16156.82 (17)
C7—C8—C9—C11171.78 (16)C13—C14—C15—C1629.09 (19)
C14—C8—C9—C10179.45 (14)C14—C15—C16—O4179.7 (2)
C7—C8—C9—C1058.35 (18)C14—C15—C16—C172.5 (2)
C2—C1—C10—C9166.58 (15)O4—C16—C17—C13152.8 (2)
C2—C1—C10—C1942.37 (17)C15—C16—C17—C1325.0 (2)
C2—C1—C10—C571.82 (17)C12—C13—C17—C16158.74 (18)
C8—C9—C10—C1176.07 (14)C18—C13—C17—C1676.7 (2)
C11—C9—C10—C154.6 (2)C14—C13—C17—C1642.0 (2)
C8—C9—C10—C1968.68 (19)C2—O1—C19—C103.4 (2)
C11—C9—C10—C1960.6 (2)C1—C10—C19—O128.71 (17)
C8—C9—C10—C556.09 (19)C9—C10—C19—O1151.40 (15)
C11—C9—C10—C5174.61 (17)C5—C10—C19—O183.62 (18)
C6—C5—C10—C1176.60 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O1i0.822.032.8088 (19)158
Symmetry code: (i) x, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC19H28O4
Mr320.41
Crystal system, space groupMonoclinic, P21
Temperature (K)295
a, b, c (Å)10.8687 (2), 6.3379 (1), 12.9038 (2)
β (°) 112.882 (1)
V3)818.93 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.20 × 0.20
Data collection
DiffractometerMAC DIP 2030K
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2065, 2065, 1929
Rint0.015
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.105, 1.14
No. of reflections2065
No. of parameters208
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.15

Computer programs: DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top
O1—C191.440 (2)O4—C161.214 (3)
O2—C21.384 (3)C1—C21.512 (2)
O3—C31.429 (3)C1—C101.528 (3)
C19—O1—C2109.44 (13)C6—C5—C4109.85 (17)
C2—C1—C10101.51 (15)C12—C11—C9113.59 (15)
O2—C2—O1108.94 (16)C18—C13—C17107.28 (17)
O3—C3—C4111.86 (18)C17—C16—C15108.98 (18)
C3—C4—C5114.94 (17)
C19—O1—C2—O2142.16 (15)C6—C7—C8—C956.6 (2)
C10—C1—C2—O141.46 (17)C10—C9—C11—C12178.96 (17)
C1—C2—C3—O363.1 (2)C11—C12—C13—C1867.1 (2)
C3—C4—C5—C6169.86 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O1i0.822.032.8088 (19)158.2
Symmetry code: (i) x, y+1/2, z+1.
 

Acknowledgements

We acknowledge financial support from the International Centre for Diffraction Data, Pennsylvania, USA.

References

First citationChampagne, D. E., Koul, O., Isman, M. B., Scudder, G. G. E. & Towers, G. H. N. (1992). Phytochemistry, 31, 377–394.  CrossRef CAS Web of Science Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationPupo, M. T., Vieira, P. C., Fernandes, J. B., da Silva, M. F. & Fo, R. E. (1997). Phytochemistry, 45, 1495–1500.  CrossRef Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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